PL193930B1 - Związki benzenosulfonyloaminowe, ich zastosowanie oraz kompozycje farmaceutyczne zawierające je - Google Patents
Związki benzenosulfonyloaminowe, ich zastosowanie oraz kompozycje farmaceutyczne zawierające jeInfo
- Publication number
- PL193930B1 PL193930B1 PL325082A PL32508298A PL193930B1 PL 193930 B1 PL193930 B1 PL 193930B1 PL 325082 A PL325082 A PL 325082A PL 32508298 A PL32508298 A PL 32508298A PL 193930 B1 PL193930 B1 PL 193930B1
- Authority
- PL
- Poland
- Prior art keywords
- amino
- chlorophenylsulfonyl
- compound
- tetrahydronaphth
- hydrogen
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 99
- 238000000034 method Methods 0.000 title description 59
- 239000000203 mixture Substances 0.000 title description 25
- AVEPGOOKZFDTOR-UHFFFAOYSA-N N=S(=O)=O.C1=CC=CC=C1 Chemical compound N=S(=O)=O.C1=CC=CC=C1 AVEPGOOKZFDTOR-UHFFFAOYSA-N 0.000 title 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 230000000694 effects Effects 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 239000004480 active ingredient Substances 0.000 claims abstract description 6
- 230000002792 vascular Effects 0.000 claims abstract description 6
- 206010020772 Hypertension Diseases 0.000 claims abstract description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 5
- 201000010099 disease Diseases 0.000 claims abstract description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 230000002829 reductive effect Effects 0.000 claims abstract description 5
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- 208000003782 Raynaud disease Diseases 0.000 claims abstract description 4
- 208000012322 Raynaud phenomenon Diseases 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
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- 208000037803 restenosis Diseases 0.000 claims abstract description 4
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 claims abstract description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 239000003937 drug carrier Substances 0.000 claims abstract description 3
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 3
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 3
- -1 4-chlorophenylsulfonyl Chemical group 0.000 claims description 46
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
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- 235000019260 propionic acid Nutrition 0.000 claims description 6
- XEYFGUPZSYKONE-UHFFFAOYSA-N 3-[6-[(4-chlorophenyl)sulfonylamino]-2-(2-nitrooxyethyl)-5,6,7,8-tetrahydronaphthalen-1-yl]propanoic acid Chemical compound C1CC=2C(CCC(=O)O)=C(CCO[N+]([O-])=O)C=CC=2CC1NS(=O)(=O)C1=CC=C(Cl)C=C1 XEYFGUPZSYKONE-UHFFFAOYSA-N 0.000 claims description 4
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- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- RGZKDSPDLWGCEN-UHFFFAOYSA-N 3-[6-[(4-chlorophenyl)sulfonylamino]-3-(2-nitrooxyethyl)-5,6,7,8-tetrahydronaphthalen-1-yl]propanoic acid Chemical compound C1CC=2C(CCC(=O)O)=CC(CCO[N+]([O-])=O)=CC=2CC1NS(=O)(=O)C1=CC=C(Cl)C=C1 RGZKDSPDLWGCEN-UHFFFAOYSA-N 0.000 claims description 2
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 claims 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 40
- 239000000243 solution Substances 0.000 description 32
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 14
- 239000003480 eluent Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
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- 238000004587 chromatography analysis Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
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- 239000011541 reaction mixture Substances 0.000 description 7
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 6
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
- 230000008602 contraction Effects 0.000 description 4
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- LLNAMUJRIZIXHF-CLFYSBASSA-N (z)-2-methyl-3-phenylprop-2-en-1-ol Chemical compound OCC(/C)=C\C1=CC=CC=C1 LLNAMUJRIZIXHF-CLFYSBASSA-N 0.000 description 3
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- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 102000008299 Nitric Oxide Synthase Human genes 0.000 description 1
- 108010021487 Nitric Oxide Synthase Proteins 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- 239000000006 Nitroglycerin Substances 0.000 description 1
- RUSLEMRHCGUNMS-UHFFFAOYSA-L O[Cr](O[Cr](O)(=O)=O)(=O)=O.C(C1=CC=CC=C1)C1=CC=NC=C1.C(C1=CC=CC=C1)C1=CC=NC=C1 Chemical compound O[Cr](O[Cr](O)(=O)=O)(=O)=O.C(C1=CC=CC=C1)C1=CC=NC=C1.C(C1=CC=CC=C1)C1=CC=NC=C1 RUSLEMRHCGUNMS-UHFFFAOYSA-L 0.000 description 1
- 241000283977 Oryctolagus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- KXXCFDDRECJGTE-UHFFFAOYSA-N [2-amino-3-bromo-6-(2-chlorophenyl)sulfonyl-5,6,7,8-tetrahydronaphthalen-1-yl]methanol Chemical compound BrC=1C(=C(C=2CCC(CC=2C=1)S(=O)(=O)C1=C(C=CC=C1)Cl)CO)N KXXCFDDRECJGTE-UHFFFAOYSA-N 0.000 description 1
- GYSVQRWSGGXROJ-UHFFFAOYSA-N [3-amino-6-(4-chlorophenyl)sulfonyl-2-trimethylsilyl-5,6,7,8-tetrahydronaphthalen-1-yl]methanol Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)C1CC=2C=C(C(=C(C=2CC1)CO)[Si](C)(C)C)N GYSVQRWSGGXROJ-UHFFFAOYSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000002744 anti-aggregatory effect Effects 0.000 description 1
- 230000000479 anti-thromboxane effect Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 210000003038 endothelium Anatomy 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229960003711 glyceryl trinitrate Drugs 0.000 description 1
- RQFCJASXJCIDSX-UUOKFMHZSA-N guanosine 5'-monophosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O RQFCJASXJCIDSX-UUOKFMHZSA-N 0.000 description 1
- 239000003126 guanylate cyclase inhibitor Substances 0.000 description 1
- 230000001435 haemodynamic effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical class CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 102000006240 membrane receptors Human genes 0.000 description 1
- 108020004084 membrane receptors Proteins 0.000 description 1
- GCNCCEAGNCVZFC-UHFFFAOYSA-N methyl 3-[6-[(4-chlorophenyl)sulfonylamino]-2-(2-nitrooxyethyl)-5,6,7,8-tetrahydronaphthalen-1-yl]prop-2-enoate Chemical compound C1CC=2C(C=CC(=O)OC)=C(CCO[N+]([O-])=O)C=CC=2CC1NS(=O)(=O)C1=CC=C(Cl)C=C1 GCNCCEAGNCVZFC-UHFFFAOYSA-N 0.000 description 1
- BSGUKBHYQITDOS-UHFFFAOYSA-N methyl 3-[6-[(4-chlorophenyl)sulfonylamino]-2-[2-(4-methylphenyl)sulfonyloxyethyl]-5,6,7,8-tetrahydronaphthalen-1-yl]prop-2-enoate Chemical compound C1=CC=2CC(NS(=O)(=O)C=3C=CC(Cl)=CC=3)CCC=2C(C=CC(=O)OC)=C1CCOS(=O)(=O)C1=CC=C(C)C=C1 BSGUKBHYQITDOS-UHFFFAOYSA-N 0.000 description 1
- KPBKSILZGUVCAV-UHFFFAOYSA-N methyl 3-[6-[(4-chlorophenyl)sulfonylamino]-3-(2-hydroxyethyl)-5,6,7,8-tetrahydronaphthalen-1-yl]propanoate Chemical compound C1CC=2C(CCC(=O)OC)=CC(CCO)=CC=2CC1NS(=O)(=O)C1=CC=C(Cl)C=C1 KPBKSILZGUVCAV-UHFFFAOYSA-N 0.000 description 1
- MTJQDYKSWQJBMA-UHFFFAOYSA-N methyl 3-[6-[(4-chlorophenyl)sulfonylamino]-3-[2-(4-methylphenyl)sulfonyloxyethyl]-5,6,7,8-tetrahydronaphthalen-1-yl]propanoate Chemical compound C=1C=2CC(NS(=O)(=O)C=3C=CC(Cl)=CC=3)CCC=2C(CCC(=O)OC)=CC=1CCOS(=O)(=O)C1=CC=C(C)C=C1 MTJQDYKSWQJBMA-UHFFFAOYSA-N 0.000 description 1
- BKEVEMYJIBAZCY-UHFFFAOYSA-N methyl 3-[6-[(4-chlorophenyl)sulfonylamino]-3-ethenyl-5,6,7,8-tetrahydronaphthalen-1-yl]propanoate Chemical compound C1CC=2C(CCC(=O)OC)=CC(C=C)=CC=2CC1NS(=O)(=O)C1=CC=C(Cl)C=C1 BKEVEMYJIBAZCY-UHFFFAOYSA-N 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 230000036963 noncompetitive effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- YLGRTLMDMVAFNI-UHFFFAOYSA-N tributyl(prop-2-enyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)CC=C YLGRTLMDMVAFNI-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9702445A FR2760235B1 (fr) | 1997-02-28 | 1997-02-28 | Nouveaux derives de benzenesulfonylamine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL325082A1 PL325082A1 (en) | 1998-08-31 |
| PL193930B1 true PL193930B1 (pl) | 2007-04-30 |
Family
ID=9504314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL325082A PL193930B1 (pl) | 1997-02-28 | 1998-02-27 | Związki benzenosulfonyloaminowe, ich zastosowanie oraz kompozycje farmaceutyczne zawierające je |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6013667A (de) |
| EP (1) | EP0864561B1 (de) |
| JP (1) | JP3917287B2 (de) |
| CN (1) | CN1160323C (de) |
| AT (1) | ATE205189T1 (de) |
| AU (1) | AU736532B2 (de) |
| BR (1) | BR9800773A (de) |
| CA (1) | CA2231026C (de) |
| DE (1) | DE69801535T2 (de) |
| DK (1) | DK0864561T3 (de) |
| ES (1) | ES2163844T3 (de) |
| FR (1) | FR2760235B1 (de) |
| GR (1) | GR3037048T3 (de) |
| HK (1) | HK1014932A1 (de) |
| HU (1) | HU224960B1 (de) |
| NO (1) | NO310068B1 (de) |
| NZ (1) | NZ329868A (de) |
| PL (1) | PL193930B1 (de) |
| PT (1) | PT864561E (de) |
| ZA (1) | ZA981681B (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2803848B1 (fr) * | 2000-01-19 | 2002-02-15 | Adir | Nouveaux derives de benzenesulfonamide, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2827280B1 (fr) * | 2001-07-13 | 2003-10-31 | Servier Lab | Nouveaux derives de benzene sulfonamide, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US8152693B2 (en) | 2006-05-08 | 2012-04-10 | Nokia Corporation | Exercise data device, server, system and method |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3000377A1 (de) * | 1980-01-07 | 1981-07-09 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue sulfonamide, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel |
| JP2558208B2 (ja) * | 1991-03-01 | 1996-11-27 | ゼリア新薬工業株式会社 | インダン誘導体及び該化合物を含有するトロンボキサン拮抗剤 |
| WO1994012488A1 (de) * | 1992-11-27 | 1994-06-09 | Byk Nederland Bv | Nitroxyverbindungen mit pharmazeutischen eigenschaften |
| FR2711139B1 (fr) * | 1993-10-15 | 1995-12-01 | Adir | Nouveaux dérivés de 1,2,3,4-tétrahydronaphtalène, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
-
1997
- 1997-02-28 FR FR9702445A patent/FR2760235B1/fr not_active Expired - Fee Related
-
1998
- 1998-02-26 JP JP04479498A patent/JP3917287B2/ja not_active Expired - Fee Related
- 1998-02-26 CA CA002231026A patent/CA2231026C/fr not_active Expired - Fee Related
- 1998-02-26 BR BR9800773-4A patent/BR9800773A/pt active Search and Examination
- 1998-02-27 EP EP98400468A patent/EP0864561B1/de not_active Expired - Lifetime
- 1998-02-27 CN CNB981080707A patent/CN1160323C/zh not_active Expired - Fee Related
- 1998-02-27 ES ES98400468T patent/ES2163844T3/es not_active Expired - Lifetime
- 1998-02-27 NO NO980842A patent/NO310068B1/no not_active IP Right Cessation
- 1998-02-27 AT AT98400468T patent/ATE205189T1/de active
- 1998-02-27 HU HU9800430A patent/HU224960B1/hu not_active IP Right Cessation
- 1998-02-27 PL PL325082A patent/PL193930B1/pl not_active IP Right Cessation
- 1998-02-27 NZ NZ329868A patent/NZ329868A/xx not_active IP Right Cessation
- 1998-02-27 PT PT98400468T patent/PT864561E/pt unknown
- 1998-02-27 DE DE69801535T patent/DE69801535T2/de not_active Expired - Lifetime
- 1998-02-27 US US09/032,587 patent/US6013667A/en not_active Expired - Lifetime
- 1998-02-27 DK DK98400468T patent/DK0864561T3/da active
- 1998-02-27 ZA ZA981681A patent/ZA981681B/xx unknown
- 1998-02-27 AU AU56360/98A patent/AU736532B2/en not_active Ceased
-
1999
- 1999-01-07 HK HK99100054A patent/HK1014932A1/xx not_active IP Right Cessation
-
2001
- 2001-10-30 GR GR20010401920T patent/GR3037048T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU9800430D0 (en) | 1998-04-28 |
| GR3037048T3 (en) | 2002-01-31 |
| ES2163844T3 (es) | 2002-02-01 |
| JPH10251217A (ja) | 1998-09-22 |
| JP3917287B2 (ja) | 2007-05-23 |
| HUP9800430A2 (hu) | 1999-06-28 |
| FR2760235A1 (fr) | 1998-09-04 |
| HK1014932A1 (en) | 1999-10-08 |
| EP0864561B1 (de) | 2001-09-05 |
| PT864561E (pt) | 2001-12-28 |
| CA2231026A1 (fr) | 1998-08-28 |
| AU736532B2 (en) | 2001-08-02 |
| US6013667A (en) | 2000-01-11 |
| FR2760235B1 (fr) | 1999-04-09 |
| NZ329868A (en) | 1999-01-28 |
| BR9800773A (pt) | 1999-12-07 |
| CA2231026C (fr) | 2004-02-10 |
| CN1195662A (zh) | 1998-10-14 |
| DK0864561T3 (da) | 2001-11-19 |
| ATE205189T1 (de) | 2001-09-15 |
| NO980842L (no) | 1998-08-31 |
| AU5636098A (en) | 1998-09-03 |
| EP0864561A1 (de) | 1998-09-16 |
| DE69801535D1 (de) | 2001-10-11 |
| NO980842D0 (no) | 1998-02-27 |
| ZA981681B (en) | 1998-09-04 |
| PL325082A1 (en) | 1998-08-31 |
| NO310068B1 (no) | 2001-05-14 |
| DE69801535T2 (de) | 2002-05-08 |
| CN1160323C (zh) | 2004-08-04 |
| HUP9800430A3 (en) | 2000-09-28 |
| HU224960B1 (en) | 2006-04-28 |
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